Head to Lakewood Ranch for Music on Main

Fans of this free concert series in Lakewood Ranch are excited that it’s returning this winter, after halting during the pandemic. It typically takes place from 6 to 9 p.m. the first Friday of each month and features, besides music, food, kids’ activities and more with a block party feel. Check the latest news at lakewoodranch.com/music-on-main.

Check Out Free Trivia Night

You’ll get plenty of atmosphere at The Mable Bar & Grill, a neighborhood pub with an eclectic clientele and crazy junk décor of old-timey lamps, chandeliers, random hockey skates and a unicorn head hanging on the wall along with all the art. Wednesday night is trivia night, so order a cold beer from the great selection and spend a couple of hours with friends. Mable’s has a surprisingly good menu and a kitchen that stays open until 1 a.m. Live music, too. Open every day, 4 p.m. to 2 a.m. 2831 N. Tamiami Trail, Sarasota, (941) 487-7373, themablebar.com.

Explore Rosemary District’s Night Market

A block of Boulevard of the Arts in the Rosemary District closes to cars for the free RADD Night Market on the third Thursday of the month from 5 to 8 p.m. through April. Local vendors serve up everything from Asian-style tacos to handmade jewelry to art. Enjoy live music while you browse. Grab a cocktail, too. 1420 Boulevard of the Arts, Sarasota

Live Music Under the Ringling Bridge

Local bands serve up Grateful Dead to soul at the Saturday night concerts put on by the funky little bait shop Hart’s Landing at Doc Werlin Park under the Ringling Bridge. The concerts are free, but the bayfront view of boats, pelicans and downtown is priceless. Set up your beach chairs on the lawn and grab a beer and a snack at the bait shop. Music goes from 7 to 10 p.m. Check Hart’s Landings’ Facebook page or call (941) 330-0650 to confirm.

Party Downtown!

Try out downtown Sarasota’s new themed events, featuring music and food the first Friday of every month along Lemon Avenue between First Street and Paul N. Thorpe Jr. Park. Called Fresh Fridays, the event will feature a dance party to a live wedding to a newcomers’ night from 8 to 11 p.m. Visit freshfridayssarasota.com.

Listen to Saturday Night Jazz Under the Stars

The Reserve Retreat on North Tamiami Trail presents live outdoor music the first Saturday of each month, at a cost of just $5, from 7:30 to 9:30 p.m. Of course, there’s food and drink available for purchase, too. Get the schedule at thereservereatreat.com/events.

Stroll St. Armands Circle

Flip-flops and beach cover-ups are perfectly acceptable for grabbing a post-sunset ice cream or gelato at Ben & Jerry’s, Kilwins, Big Olaf or Settimi’s and then taking a leisurely stroll to browse the shops. Free parking on weekends and holidays and only 50 cents an hour in the parking garage.

Waste Away at Downtown’s Waterfront Tiki Bar

For vacationing out-of-towners and townies who want to feel like they’re on vacation, O’Leary’s Tiki Bar & Grill has a tropical beachy vibe at downtown’s Bayfront Park, with live music booked every night. Order a beer on draft and a kraut dog and then sit under the huge tiki hut, or bring your own beach chair. Well-behaved dogs are welcome and so are kids, who can head to the kids’ fountain or playground. 5 Bayfront Drive, Sarasota, (941) 953-7505, olearystikibar.com.